高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (01): 71.doi: 10.3969/j.issn.0251-0790.2012.01.012

• 有机化学 • 上一篇    下一篇

Globo H四糖衍生物的高效合成

魏国华1,2, 杜宇国1, Khushi L. Matta2   

  1. 1. 中国科学院生态环境研究中心, 环境化学与生态毒理学国家重点实验室, 北京100085;
    2. Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA
  • 收稿日期:2011-02-13 出版日期:2012-01-10 发布日期:2011-12-20
  • 通讯作者: 魏国华,男,博士,副研究员,主要从事寡糖药物的设计合成研究.E-mail:wgh@rcees.ac.cn E-mail:wgh@rcees.ac.cn
  • 基金资助:

    国家"重大新药创制"科技重大专项(批准号: 2009ZX09501-011)资助.

Highly Efficient Synthesis of Two Globo H Tetrasaccharide Analogues

WEI Guo-Hua1,2, DU Yu-Guo1, Khushi L. Matta2   

  1. 1. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China;
    2. Cancer Biology, Roswell Park Cancer Institute, Buffalo, NY 14263, USA
  • Received:2011-02-13 Online:2012-01-10 Published:2011-12-20
  • Contact: WEI Guo-Hua E-mail:wgh@rcees.ac.cn

摘要:

设计合成了2个Globo H四糖衍生物1和2, 将其作为标准样品可用于研究β1,3-葡萄糖醛酸(GlcA)转移酶及GlcA-3-O-硫酸化(Sulfo)转移酶在肿瘤组织内的特异性表达.

关键词: Globo H, 糖基转移酶, 硫酸化转移酶, 葡萄糖醛酸, 2-萘甲醇

Abstract:

The synthesis of two  Globo H tetrasaccharide analogues,  allyl O-(β-D-glucopyranosyluronic acid)-(1,3)-O-(β-D-galactopyranosyl)-(1,3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1,3)-O-α-D-galactopyranoside and allyl O-(3-O-sulfo-β-D-glucopyranosyluronic acid)-(1,3)-O-(β-D-galactopyranosyl)-(1,3)-(2-acetamido-2-deoxy-β-D-galactopyranosyl)-(1,3)-O-α-D-galactopyranoside,  were described.  Construction of the target molecules was achieved through a key combination of BF3·Et2O and trichloroacetimidate glycosylation methodology.  This is the first report on the synthesis of these derivatives,  which could be used as potential novel substrates and reference samples for the study of β1,3-glucuronosyltransferase and GlcA-3-O-sulfotransferase in cancer tissues.

Key words: Globo H, Glycosyltransferase, Sulfotransferase, Glucuronic acid, 2-Naphthylmethyl

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